Yellowish-green triphenylmethane dye.



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Ji l ii is oasis n MAX 'WEILEE OF ELBEBFELD, GEEMANY, ASSEG-NOR TOSYN'THETItZ PATENTS CG, I

INQ, 0E NEW' YORK, l\l. Y., A. CORPORATION OF NEW YORK.

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No Drawing.

YELLOWISH-GREEN rnrrHnnYLMETHANE DYE.

Pa-tented June 3d, 1914.,

Application filed July 17, 1913. Serial No. rzaesz.

To all whom it may concern Be it known that 1, MAX "WEILER, doctor ofphilosophy, chemist, citizen of the German Empire, residing atElberfeld, Gelinany, have invented new and useful I1nprovenients inYellowish-Green Triphenylmethane Dye, of which the following is aspecification.

i have found that new and valuable coloring matters of thetriphenylmethane series can beobtaincd by condensing sultonic acids ofallcylizcd or arallzylised nicta-toluidins or mixtures thereof witharomatic aldehydcs containing no allqylamino group in para position tothe carbonyl group and oxidizing the resulting leuco compounds orcondensing the said an'iins with the aldchydes, sult'onating andoxidizing the leuco compounds. These coloring matters have aconstitution graphically represented as follows:

R a 0. il

where R and R are the radicals or residues of nicta-toluidinssubstituted in the amino group, e. 9., by alkyl or aralli'yl radicals,and R an aromatic radical or residue which may or may not be substitutedby alkyl, sulfonic or other groups, halogen, etc.

The new dyes are after being dried and pulverized in the shape oil theiralkaline salts dark powders soluble in Water generally with They aredistinguished from the known coloring matters otthis series byfurnishing green shades on wool of a yellow tint which could hithertoonly be obtained with mixture of green triplicnylinethane' dyes withother yellow coloring matters. The shades thus ohta incd possess a goodfaslncss to alkali and -tolling.

In order to illustrate the new process more fully the following exampleis given, the parts being by weight :-245 parts ofethyll)cnzyl-mctatoluidin-sulfonic acid (sodium salt) are boiled during70hours together with 920 parts of water, 111.6 parts of suli uricaci'd(60 36,), 100 partsot alcohol and 71 parts of ortho-chlorobenzaldehyde.The leuco acid separates as a solid, it is fil tcrcd oil, dissolved insodium carbonate solution and oxidized with Pb O, and sulfuric acid. Thenew coloring matter havingin a tree state most probably the formula:

hyde, 2-chloro 5 sulfobcnzaldeliyde, Inetaoxybcnzaldehydc or on theother hand dicthyi-ineta-toluidin, etc.

I claim I -1. The new dyes of the triphcnyhnethane seriesbeingsulfonicacids derived from an aromatic aldehyde and a mcta-tolu1dm sub stitutcdin the amino group having the fol-' lowing graphically representedconstitution:

where R andR' arc the radicals of 1nctatoluidins substituted in theamino group, and R an aromatic radical, which dyes are after being driedand pulverized in the shape of their alkaline salts dark powders solublein water generally with a yellowish-green coloration; dyeing wool greenshades distinguished by their yellowish tint fast to a yellowishgreencoloration.

alkali and to fulling, substantially as de-' scribed.

2. The new dyes of the triphenylrnethane series being sulfonio acidsderived from a halogen substituted aromatic aldehyde and a meta-toluidinsubstituted in the amino group, having. the following graphicallyrepresented constitution:

wherdR and R are the radicals of nietatoluidins substituted in the aminogroup, and

R a halogen substituted aromatic radical, which dyes are after beingdried andpulverized in the shape of their alkaline salts I dark powderssoluble in water generally vith a yellowish-green. coloration; dyeingWOOl green shades distinguished by their yellowish tint fast to alkaliand to fulling, substantially as described.

3. The new dyes. of the triphenylinethane series being sulfonicacidsderived from an aromatic aldehyde and a Ineta-toluidin substituted inthe amino group having the 01 lowing graphically representedconstitution:

where R is a substituted aromatic radical which are after being driedand pulverized green powders soluble in water with a yellowish-greencoloration and dyeing vwool where R and R are the radicals ofrnetatoluidins substituted in the amino group and R a substitutedaromatic radical, which dyes are after being dried and pulverized in theshape of their alkaline salts dark powders soluble in water generallywith a yellowish-green coloration; dyeing wool green shadesdistinguished by their yellowish tint R a chlorwubstituted aromaticradical which dyes are after being dried and pul-' verized in the shapeof their alkaline salts dark powders soluble in water generally with ayellowish-green coloration; dyeing wool green shades distinguished bytheir yellowish tint fast to, alkali and to iulling substantially asdescribed.

5. Thenew dyes having in a free state the formula graphicallyrepresented yellowish-green shades fast to alkali and to fulling,substantially as described.

6. The new dye having in a free state most probably the formula:

CgHs CH8\/\%N CH3-C6H4-$0Q which is after being dried and pulverized agreen powder soluble in water with a yellowish-green coloration anddyeing wool yellowish-green shades fast to alkali and to fulling,substantially as described.

In testimony whereof I have hereunto set my hand in the presence "of twosubscribing witnesses. v I

MAX WEILER. [n s] Witnesses.

ALBERr NU'FER, H. SIMONS.

Copies of this patent may be obteinedfor five cents each, byaddressing'the commissioner o 2etei1te,

, weahingtoml. G."

